Find Deals on Flights from Caribbean to Chicago

Depart
Return
1 adult
Adults
18-64
Seniors
65+
Youths
12-17
Children
2-11
Seat Infants
under 2
Lap Infants
under 2
Students
under 26
The price shown for each flight will be the average for all passengers including any infants.
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Dates flexible? Here are the best fares found in the past 48 hours...

Book cheap flights from Caribbean to Chicago

(Round-trip)
Depart: Wed Mar 1 2017 Return: Tue Mar 14 2017 Trip spans 13 days
Major Airline
Major Airline
SJU
ORD
6h 55m
nonstop
ORD
SJU
24h 08m
nonstop
Depart: Mon Jan 30 2017 Return: Mon Feb 6 2017 Trip spans 8 days
Spirit Airlines
Spirit Airlines
SJU
ORD
13h 49m
1 stop
ORD
SJU
13h 39m
1 stop
Depart: Wed Mar 1 2017 Return: Mon Apr 3 2017 Trip spans 33 days
JetBlue
JetBlue
SJU
ORD
27h 00m
1 stop
ORD
SJU
12h 10m
1 stop
Depart: Tue Feb 14 2017 Return: Mon Feb 20 2017 Trip spans 7 days
United
United
SJU
ORD
9h 59m
1 stop
ORD
SJU
4h 25m
nonstop
Depart: Wed Mar 1 2017 Return: Mon Mar 6 2017 Trip spans 6 days
American Airlines
American Airlines
SJU
ORD
5h 27m
nonstop
ORD
SJU
8h 53m
1 stop
Depart: Wed Feb 15 2017 Return: Mon Feb 27 2017 Trip spans 13 days
Delta
Delta
SJU
MDW
9h 25m
1 stop
MDW
SJU
6h 22m
1 stop
Depart: Sun Mar 5 2017 Return: Tue Mar 21 2017 Trip spans 16 days
Frontier
Frontier
PUJ
ORD
5h 17m
nonstop
ORD
PUJ
4h 38m
nonstop
Depart: Sat Feb 4 2017 Return: Mon Feb 6 2017 Trip spans 3 days
Major Airline
Major Airline
SJU
ORD
14h 42m
nonstop
ORD
SJU
25h 08m
nonstop
Depart: Thu Feb 16 2017 Return: Mon Feb 20 2017 Trip spans 5 days
Spirit Airlines
Spirit Airlines
SJU
ORD
19h 18m
1 stop
ORD
SJU
18h 33m
1 stop
Depart: Tue Feb 14 2017 Return: Fri Feb 17 2017 Trip spans 4 days
Major Airline
Major Airline
SJU
ORD
7h 53m
nonstop
ORD
SJU
15h 50m
nonstop
Depart: Thu Feb 2 2017 Return: Wed Feb 8 2017 Trip spans 7 days
JetBlue
JetBlue
NAS
ORD
5h 11m
1 stop
ORD
NAS
9h 56m
1 stop
Depart: Wed Jun 14 2017 Return: Wed Jun 21 2017 Trip spans 8 days
American Airlines
American Airlines
SJU
ORD
5h 02m
nonstop
ORD
SJU
8h 46m
1 stop
Depart: Tue Feb 21 2017 Return: Wed Mar 22 2017 Trip spans 29 days
United
United
BQN
ORD
9h 54m
1 stop
ORD
BQN
7h 51m
1 stop
Depart: Wed Mar 1 2017 Return: Mon Mar 6 2017 Trip spans 6 days
Delta
Delta
SJU
MDW
9h 30m
1 stop
MDW
SJU
6h 54m
1 stop
Depart: Wed Apr 26 2017 Return: Mon May 1 2017 Trip spans 6 days
JetBlue
JetBlue
SJU
ORD
9h 49m
1 stop
ORD
SJU
8h 28m
1 stop
Depart: Wed Mar 1 2017 Return: Sun Mar 5 2017 Trip spans 5 days
United
United
BQN
ORD
8h 43m
1 stop
ORD
BQN
9h 45m
1 stop
Depart: Fri Apr 28 2017 Return: Sat Apr 29 2017 Trip spans 2 days
Major Airline
Major Airline
SJU
ORD
6h 56m
nonstop
ORD
SJU
6h 44m
nonstop
Depart: Thu Mar 2 2017 Return: Sun Mar 5 2017 Trip spans 4 days
Delta
Delta
SJU
MDW
8h 28m
1 stop
MDW
SJU
8h 08m
1 stop
Depart: Mon Apr 24 2017 Return: Sun Apr 30 2017 Trip spans 7 days
Spirit Airlines
Spirit Airlines
BQN
ORD
9h 22m
1 stop
ORD
BQN
7h 44m
1 stop
Depart: Tue May 9 2017 Return: Tue May 23 2017 Trip spans 15 days
JetBlue
JetBlue
SJU
ORD
8h 47m
1 stop
ORD
SJU
8h 30m
1 stop
* Prices are per person and are for e–tickets and include all taxes & fees in USD.

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Here's why:

We’re not the seller.
At KAYAK we don’t set the prices, so it’s not possible for us to guarantee what other companies are selling.

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Our service lets you quickly and easily compare results from hundreds of travel sites at once. In this sense, KAYAK is a search engine and we can't guarantee prices we find.

Why aren’t prices accurate 100% of the time?
Prices on airline seats, hotel rooms and car rentals can change frequently. Several people may also be trying to buy the same travel option simultaneously. As a result, you may find, on occasion, that certain prices are no longer available.

If you have more questions or if you have a bad price to report to us,
please send us an email and someone from our team will get back to you promptly.

Airports
Origin

Aguadilla
$309
Nassau
$281
San Juan
$249
Punta Cana
$410
Destination

Chicago
only $249
only $311
Airlines Airline reviews

38 travelers who booked a flight from San Juan to Chicago rated their chosen airlines with an average of 8.0.

Overall
8.3
Boarding
8.1
Crew
8.2
Comfort
8.3
Food
7.4
Entertainment
7.6